Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-ethylbenzonitrile

HRID 1951384Notes

Reaction equation

HRID 1951384 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH:11]=O)[C:6]#[N:7])[CH3:2].[CH3:13][C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17].C(O)(=O)C.N1CCCCC1>ClCCl>[C:16]([C:15]([C:14](=[O:19])[CH3:13])=[CH:11][C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:1][CH3:2])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 178193273-Ethyl-4-formylbenzonitrile

Product 1

HCID 596030134-(2-Acetyl-3-oxobut-1-en-1-yl)-3-ethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

885 mg (5.55 mmol) of 3-ethyl-4-formylbenzonitrile, 0.62 ml (6.11 mmol) of 2,4-pentanedione, 0.47 ml (8.33 mmol) of acetic acid and 0.11 ml (1.11 mmol) of piperidine in 40 ml of anhydrous dichloromethane are stirred under reflux with a water trap for 24 h. After cooling, the reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue (1.07 g) is reacted further without further purification.

Workup

  1. temperatureunder reflux with a water trap for 24 h
  2. temperatureAfter cooling
  3. washthe reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue (1.07 g) is reacted further without further purification

Sources & evidence

ORD record
ord-c4b2be65e5b043e8b5b9f6fc349844ea
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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